Dimethylformamide → HCID 4186278, compound
Reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)=[CH:9][CH:8]=1.[OH-].[Na+].CN(C)[CH:26]=[O:27]>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH:26]=[O:27])=[CH:11][CH:12]=1Participants
Procedure
In a 100-ml round-bottom flask is placed 2.8 mL of dimethylformamide (2.74 g, 3.74 mmol). The flask and the content was cooled in an ice-salt bath for about 0.5 hour and 0.86 mL (1.44 g, 94 mmol) of freshly distilled phosphorusoxychloride is subsequently added with stirring to the dimethylformamide dropwise. Then a solution of 1.0 g of 2 (85 mmol) in 1 mL of dimethylformamide is added to the above solution slowly. After the addition, the temperature of the solution is brought to 40° C. and allowed to stir for an hour. At this time, 1 N NaOH (10 mL) was added to the reaction mixture dropwise. The resulting mixture is heated rapidly to the boiling point and allowed to cool to room temperature. The resulting precipitate is collected on a filter and the solid was further washed with water. Compound 3 obtained from this procedure was pure enough for the next reaction. MS (Es+ve) m/z 300, (Es−ve) m/z 298.
Workup
- customIn a 100-ml round-bottom flask is placed
- temperatureThe flask and the content was cooled in an ice-salt bath for about 0.5 hour
- additionAfter the addition
- customis brought to 40° C.
- temperatureThe resulting mixture is heated rapidly to the boiling point
- customThe resulting precipitate is collected on
- filtrationa filter
- washthe solid was further washed with water
Sources & evidence
- ORD record
- ord-3508e7c90aee4f4eaa5f23acb02c29e3
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08980895B2
Reaction notes
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